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Used in Historic Textiles by Means of Uv-Vis Spectrophotometry and Ft-Ir Spectroscopy

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Used in Historic Textiles by Means of Uv-Vis Spectrophotometry and Ft-Ir Spectroscopy 153 CHARACTERIZATION OF COLOURING COMPOUNDS IN ANNATTO (BIXA ORELLANA L.) USED IN HISTORIC TEXTILES BY MEANS OF UV-VIS SPECTROPHOTOMETRY AND FT-IR SPECTROSCOPY. Dolores Julia Yusá-Marco1, María Teresa Doménech-Carbó1, Ivan Lucio Vaccarella1, Antonio Fernando Batista dos Santos1, Sofia Vicente-Palomino2 and Laura Fuster-López3 Instituto Universitario de Restauración del Patrimonio de la Universidad Politécnica de Valencia 1 Laboratorio de análisis físico-qímico y control medioambiental de obras de arte 2 Taller de materiales arqueológicos y etnográficos 3 Taller de análisis y actuación en pintura de caballete y retablos CORRESPONDING AUTHOR: Dolores Julia Yusá-Marco, [email protected] ABSTRACT: Valencian historic textiles were commonly woven with coloured silks and natural dyes in the 18th century. The opti- misation of analytical methods to extract and classify the dyes used is required to understand not only their degradation process, but also the state of conservation of these textiles. This paper shows the results obtained in the optimisation of the preparation process of the two main colouring components in annatto (Bixa Orellana L.), namely, bixin and norbixin, prior to analysis by means of UV-Vis Spectrophotometry and FTIR spectroscopy. The results of the analysis were also satisfactor KEYWORDS: natural Dyes, carotenoids, annatto, Bixa Orellana L, silk, FTIR spectroscopy, UV-Vis spectrophotometry number of carotenoid compounds that constitute the main colouring 1. INTRODUCTION agents: bixin is the predominant colouring compound in liposoluble preparations, and its chemical structure is shown in Figure 1. Natural dyes obtained from plants, animals and minerals have been Norbixin (see also Figure 1), which can be obtained by means of historically combined according to ancient procedures and recipes bixin saponification, is the main colouring agent in hydrosoluble and have resulted in a wide spectrum of tones and shades. preparations. Nevertheless, norbixin can also be found in both seeds and liposoluble solutions. In the 18th century, dyes were classified into two groups according to their inherent characteristics and quality. The first group consisted Annatto colouring compounds can be identified by UV-Vis of the colourants considered ‘major or good dyes’ (‘tinte mayor o Spectrophotometry and FTIR Spectrometry. Devia developed bueno’), whereas the second group comprised dyes known as ‘minor an extraction method to determine the maximum absorption or false dyes’ (‘tinte menor o falso’). Those of the latter group were wavelength of annatto dyes. It consisted of 1gr of annatto dye seeds used “as base-dyes to obtain specific shades and also more affordable in a 100 ml-calibrated flask containing a 5% KOH solution. Then, mixtures. At other times, they were also used alone, but they were 1 ml aliquot of this solution was transferred to a second calibrated considered low-quality materials” (Roquero, 2006). flask (100 ml), which also contained a 5% KOH solution. The absorption spectrum finally obtained was in the range of between Annatto, the dye obtained from the Bixa Orellana L., was considered 300nm and 600nm (Figure 2). a “minor” dye. Joseph Macquer’s treatise refers to annatto as a weak material that changed and deteriorated easily. He also stated that “its Absorption bands with a maximum value at 450nm for the dye colours are so beautiful, and this is the only reason to use them since beauty is extracted from annatto (bixin) can be obtained as referred to in the preferred to duration when it comes to dyeing silks” (Macquer, 1771: 107). literature (Mosquera, 1989; Devia and Saldarriaga, 2003: 8 and Devia, 2005), and at 483 nm for norbixin (Natukolor, 2004). The UV- Given the beauty of the yellow and orange tones obtained with Vis spectrum of annatto was reported by Britton (Briton, 1995), which annatto, and despite being classified as a “minor” dye, it was widely is dominated by an absorption band with three maximum values. used for silk dyeing in Spain. Indeed, eighteenth-century textiles are a good example of this practice. Additionally, Devia developed the IR analysis of annatto dye seeds in the following way: pressed KBr powder is prepared with Dye treatises from the 18th century included a wide range of the coloured powder and the infrared spectrum is obtained (Devia, tones that could be obtained from annatto pure dye or diluted at 2005)). Devia indicates: “a band close to 1600 cm-1 can be observed that different concentrations. The combination of annatto with other represents the stretching vibration of the -C=O groups (typical of bixin colourants also produced all types of warm colours ranging from structures). Moreover, several consecutive bands can be observed in the area gold to maroon, which were reported in the treatises of that period between 1700 and 1800 cm-1, that are found typically in double bonds which (Fernández, 1995: 51). are usually present in the organic structures that characterise bixin” (Devia and Saldarriaga, 2003: 8). Annatto is a natural dye obtained from a tropical plant growing in America. Its seeds are covered by a red resin which contains a ARCHÉ. PUBLICACIÓN DEL INSTITUTO UNIVERSITARIO DE RESTAURACIÓN DEL PATRIMONIO DE LA UPV - Núm. 3 - 2008 154 Dolores Julia Yusá-Marco, María Teresa Doménech-Carbó, Ivan Lucio Vaccarella, Antonio Fernando Batista dos Santos, Sofia Vicente-Palomino, Laura Fuster-López Figure 1. Chemical structure of bixin and norbixin carotenoids, cis and trans isomers and Figure 2. UV-Vis spectrum of annatto extracts from solid dye seeds (Devia, 2005) their main degradation products (Scotter, 1995) Extracting the colouring compounds from the fabric (silk in this case) out prior to the spectroscopic characterisation of annatto colouring prior to analysing by spectroscopic techniques is required to identify compounds. Two types of extraction processes have been evaluated. natural dyes in historic textiles. Thus, several methods have been The first method was carried out in two stages: acid hydrolysis proposed for this purpose. Among them, it is worth mentioning that followed by extraction with organic solvents. The second method is of Orska-Gawrys et al (2003: 239), which uses a mixture of ethanol simpler than the first, and consists of direct extraction with organic and hydrochloric acid for the hydrolysis stage. Chloro-solvents such solvents without the need for a previous acid hydrolysis stage. as dichloromethane can be used for direct extraction, as suggested by Tocchini and Mercadante (2001: 310). Other authors, however, Secondly, the colouring compounds extracted from the dyed propose the use of dimethylformamide and acetic acid for the direct textiles were characterised by UV-Vis Spectrophotometry and extraction of synthetic dyes from cotton fibre (Chao et al, 1998: 59). FTIR spectrometry. The assignment of the main absorption bands in the UV-Vis-IR regions allowed us to not only differentiate the Being a proteinaceous material, silk can be affected by acid or basic different colouring compounds present in the dyed textiles, but to environments that deteriorate it as a result of the hydrolysis process. also evaluate the efficiency of the extraction method tested. The typical functional groups contained in their amino acids, which are present in the coloured extracted solution, can be identified by 2. EXPERIMENTAL FTIR. 2.1. Reagents and Reference Materials As Becker states: “Over 80% of the fibroin molecule consists of glycine, alanine and serine in a 3:2:1 ratio. The highly repetitive sequence of fibroin The chemical reagents and solutions used were ethanol, 96%, pa, is described by: Gly-Ala-Gly-Ala-Gly-Ser-Gly-Ala-Ala-Gly- [Ser-Gly-(Ala- Panreac; hydrochloric acid, 37%, pa, Carlo Erba; Dichloromethane Gly) -]8-Tyr, where n is usually 2”. (Becker et al, 1997:27). The chemical n (DCM), pa, Carlo Erba; Chloroform, 99+%, Acros; Ethanol: structure of these amino acids is characterised by the existence of hydrochloric acid 3M (1:1) solution. Acetonitrile (ACN) and Methanol primary amides. (MeOH), HPLC-gradient grade, Carlo Erba; Potassium bromide, 99+%, RS, Aldrich; Trifluoroacetic acid (TFA) 99% (Panreac); Seok Ki et al. developed the structural characterisation of silk by Acetic acid 100% (Prolabo), Dimethylsulfoxide (DMSO), RS, Carlo means of several analytical techniques such as FTIR: “Protein Erba, Deionised water, HPLC grade, Medica Elga (Eolia Water). HCl conformation is determined by identifying the peak positions of amide I, II, 3M:MeOH:H O (2:1:1) solution and MeOH:H O (1:1) solution and III corresponding to C=O, N-H, and C-N stretching, respectively. All 2 2 regenerated silk filaments present amide I and II peaks at around 1630 and Annatto seeds (ref. 37350) were provided by Kremer pigmente 1520 cmí1, as well as an amide III peak at 1260 cmí1 as a shoulder peak, thus (Figure 3). indicating the ȕ-sheet structure known as silk II type. On the other hand, SS powder presents amide I and II peaks at slightly different positions (1623 and The experiments were performed on 100% silk, whose commercial 1516 cmí1) with the absence of a shoulder peak at 1260 cmí1. This is probably name was ponge textile, supplied by Soditex, S.L.. This textile was due to an aggregation of SS molecules, and not to ȕ-sheet conformation.” characterised (Vicente-Palomino et al, 2006: 139) as: (Seok Ki et al, 2007: 346) 2.2. Instrumentation This research shows the earliest results obtained in the optimisation of the extraction process of the two main colouring components of UV-Vis Spectrophotometry. The spectra in the UV and visible region annatto, bixin and norbixin, from silk textiles which was carried were measured with a HITACHI U2010 recording double-beam Number of yarns Density (taffeta) Name Composition Fabric grammage warp weft warp weft Pongee 100% Silk 7 tex 4 tex 60 60 0’00459g/m2 Table 1 Characterization of textile. ARCHÉ. PUBLICACIÓN DEL INSTITUTO UNIVERSITARIO DE RESTAURACIÓN DEL PATRIMONIO DE LA UPV - Núm.
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